Hydrogen Sulfide → 2-Thioadenosine

HRID 917839

反応式

HRID 917839 の反応式
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[Na].[SH2:22]>CN(C)C=O.O.C(O)(=O)C>[CH:7]1[N:8]([C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[C:18]2[C:5](=[C:4]([NH2:20])[NH:3][C:2]([N:19]=2)=[S:22])[N:6]=1

参加物

7

反応物 3

HCID 402Hydrogen SulfideHCID 89742-ChloroadenosineHCID 5360545Sodium

生成物 1

HCID 64519652-Thioadenosine収率 100%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

2.0 g of 2-chloroadenosine was dissolved in a solution of 20 ml of anhydrous hydrogen sulfide and 1.5 g of sodium metal in 80 ml of dimethylformamide, and the mixture was allowed to react at a temperature of 80°C for 5 hours under anhydrous conditions. The reaction mixture was then diluted with 80 ml of water and neutralized with acetic acid followed by concentration. The resulting concentrate was dissolved in 75 ml of a mixture of n-butanol and water (2:1 by volume), and 25 ml of acetic acid was added to the solution. After allowing the mixture to cool, the precipitated crystals were filtered to obtain 21 g (100% yield) of crude 2-thioadenosine. The product thus-obtained was dissolved in dilute aqueous ammonia and adjusted to a pH of 4 with acetic acid to obtain pure 2-thioadenosine having a melting point of 196° ~ 199°C (with decomposition).

後処理

  1. customto react at a temperature of 80°C for 5 hours under anhydrous conditions
  2. concentrationfollowed by concentration
  3. concentrationThe resulting concentrate
  4. dissolutionwas dissolved in 75 ml of a mixture of n-butanol and water (2:1 by volume), and 25 ml of acetic acid
  5. additionwas added to the solution
  6. temperatureto cool
  7. filtrationthe precipitated crystals were filtered

出典と根拠

ORDレコード
ord-2c8431e780274999a5c7c6c810700adf
出典データセット
uspto-grants-1976_07
特許番号
US03968102

関連ノート

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